The Power Of No, Part 1: Oprah Winfrey

There’s incredible power in saying “yes.” It opens up avenues and allows us to be brave. In Cheryl's case, it’s what led to her becoming Sugar. But saying yes to life's opportunities can also have its risks.

This week, the Sugars are joined by Oprah Winfrey to discuss when to say no, how to say no, and what happens in the wake of that.

Dear Sugars,

I am a young, female writer working a relatively powerful job publishing, teaching on the side, and at the same time, trying to finish my own book. I'm so lucky to be where I am, and while plenty of it is thanks to my own hard work, plenty of it is thanks to the mentors and teachers who helped open doors for me, who took my ambitions seriously and knew first-hand the subtle and insidious ways being a woman would be counted against me and did what they could to help me rise regardless. Even if I hadn't had these kinds of mentors, I would feel a moral obligation to support the women around me and help them rise, too.

Now, I'm at last in a position where I can really do this. But the demands on me to do so feel relentless, exhausting and thankless. I feel like the more I help the people around me rise, the more and more I get diminished and ground down. I get asked to do four to five informational interviews a month, to read people's work for free and donate my own writing, to write dozens upon dozens of recommendation letters. My male colleagues get asked for the same to some degree, but not with the same relentlessness, and they don't seem to have the same problem saying no. Often if I'm not the one to, say, recommend an intern or take her out for lunch to talk about jobs, it simply won't happen. And so I say yes to nearly all of it, and I hate it.

I haven't really written in almost a year. I genuinely want to help, particularly when the requests come from younger women, and if time and energy were infinite, I would be glad to do all these things. But they're not, and I'm miserable. Add to this a work culture where the few women on the staff do the vast majority of the work with the least credit and the least pay, where, in spite of all the fight I've put into getting where I am, I'm still not taken seriously and I'm left feeling beat.

Sugars, how do I keep from burning out? How do I help support the women around me without losing track of my own work? And how do we even begin to shift this whole culture so we stop being appalled when women say “no,” but rather, give them the space to really say “yes?”

Signed, The door is open, but I'm still knocking

Cheryl Strayed: I could have written a version of this exact letter. I am with you, TDIOBISK. This is a piece of advice that I can give you: You are helping those younger women, and there's a limit to the number of them that you can help. That's actually been useful to me to say — that I'm not going to stop entirely, though I have gone through periods where I've said “I'm taking a break.” I think that's one approach, but you can also set a limit. I think the deeper thing for me, and probably for you too, is that you need to come to terms with this sense of shame and apology you have about having needs of your own.You can't feel apologetic about the most important things in your own life.

Steve Almond: What's really striking is that, in this note you write, "I haven't really written in almost a year." If you really want to set a good example for younger women, or just women in general, do it by doing your work and putting your work at the top of the list of things that you need to get done each day.

Cheryl: These women see your success, so they want to talk to you and have these informational meetings. But you have to set boundaries. Saying “no” is a boundary. Some people are going to be offended by that, but some people will be inspired by it. I have said this time and time again: so much of what I think of as good and positive and powerful and meaningful in my life came about because I said "yes." I want to help other people. I'm naturally a helper. But what I've come to realize is that, if I don't learn how to disappoint people by saying “no” to them, I will be devoured. I love saying “yes” in part because that's how I've been so successful in getting love, not just successful in my career. I realized I had to let go of this idea of myself as somebody whom everyone's going to love.

Steve: Part of the dynamic that we're going to explore is a power relationship. In those moments where people ask us for something, they're really coming on bended knee. When you say “no,” that power dynamic becomes laid bare in a negative way. You can try to be polite about it, but it's still a “no.”

Cheryl: TDIOBISK, you signed your letter “the door is open,” but you need to shut the door and set a boundary between you and all of the people who would rather get something from you now than wait for the next thing you have to give. So close that door. We wish you luck.

Dear Sugar,

I'm bad at saying “no.” I'm a people-pleaser and a perfectionist, but I'm on the road to recovery. Almost exactly a year ago, the universe broke the dam, and the “no”s came pouring out of me. It was the dawn of a new era — the "me" era — both for the better and for the worse. My closest relationships haven't been the same since. I know in my heart that the better outweighs the worse, but what pains me are the relationships that didn't survive. They are mainly my family relationships, the ones we assume are unconditional.

I come from a family of five: mom, dad, oldest daughter (me), second daughter, and a younger brother. My dad is an immigrant: strict, tyrannical, and now a painfully distant courtesy call on holidays and birthdays. My mom is a former artist who would always ride the highs and lows of life with abandon.

The three of us kids became relatively close, and we were very close to our mom, united against our common enemy, our dad. In high school, I found out my mom had been suffering from depression for some time. I tried desperately to keep the family together and, also, to keep her alive after two suicide attempts. I found myself supporting my siblings emotionally and, eventually, financially. I've always been the responsible one, and I can admit I liked being able to help. But I was gradually handing over my life as the burden grew.

So one year ago, I started living my life. I said “no” to a romantic relationship that was holding both of us back for the greater part of seven years. I said “no” to funding my brother in school when he wasn't even going to class. I said “no” to my sister who wasn't keeping track of how many loans she had taken from me and was using them to travel the world for fun, knowing she'd need to ask for more money later. It isn't the money that upsets me, it's the assumption that I was the safety net, no questions asked. I even got attitude a few times when I mustered the courage to express my concerns. Most painful of all, I said “no” to my mom. I said “no” to my mom who loved us all so much, who wanted us to be safe and happy and who blamed herself for our struggles because of her own, and for the unhappy marriage in which she chose to remain. I couldn't be a dumping ground for pain and despair anymore.

Within a week, each one of them cut me off. I lost the three people I loved most in the world in one fell swoop, all because I stood up for myself. I went through all the stages a victim of ghosting does: I thought it was a mistake, I panicked that something had gone terribly wrong, I started to see the truth, I got angry, I got sad and, finally, I started to heal. The one brilliant, bright light that I've gotten from all of this is that I'm finally, finally living my life. As you can see, Sugars, I'm slowly building my “‘no’ muscles.”

My question isn't how to say “no,” but, rather, how to deal with the aftermath. I'm grateful that my sister and I have begun to rebuild our relationship based on open communication and a more balanced give-and-take. The others are still mostly M.I.A. I struggle with the guilt associated with the consequences of saying “no.” Would my brother have had a better chance of securing a full-time job and gaining independence if I had funded his unpaid internship stint away from home for a few months? I've only gotten a cryptic two or three word text reply from my mom. In the past year, she's only spoken with me on the phone once, on Christmas Day, when she said things were not going well in a mic-drop kind of way, and left it at that. I know she's not in a good place, and I'm not the only one she's cut out.

How do I support her while using “no” to build healthy boundaries? I feel guilty that I feel happier and healthier now that she's not in my life. I'm also deeply saddened that we're not sharing the beauty of our lives with each other, both the good and the bad. I think she would be proud of who I've become. I don't want to wait until time has run out to realize my regret for not having tried hard enough to show her that I love her and to tell her that the silence hurts. What do I do now that the storm has cleared?

Signed, Ghost of No

Steve: This letter speaks so deeply to not just saying “no” to family, but the aftermath of that “no.”

Cheryl: Here's another letter that I really relate to. Sometimes in order to mend your own heart, you actually have to cut a thread with someone who means something to you. I think you made the absolute right decision, Ghost of No. Already you're seeing a healthier bond with your sister, and when we're in relations with other people, they have to do their work too. The best advice I can give is, keep making the right choices for yourself, and when you do that, people who are making the right choices for themselves can have relationships with you.

Oprah Winfrey: I related to Ghost of No because, first of all, there is always this innate fear that, if I say “no,” I'm going to somehow be discarded or dismissed or unloved. That started early for me, and it's probably the reason why I was abused. There was a vulnerability and a lack of knowingness about my own boundaries and my own personhood that other people could see. But if a person turns against you because you say “no” to them, you recognize that that wasn't real love anyway. True love, true friendship, true support comes from people who want you to tell your own truth. They don't want things given to them that don't come from a pure place. Ultimately, you have to let go of some of the toxicity in your life that was preventing you from being your most true self in the first place, even with family members.

Cheryl: How did you learn how to say “no?”

Oprah: I started small. For me, it was actually a real call from Stevie Wonder asking me to participate in an event. He was raising money for a child who needed open heart surgery, and he was doing a concert. I thought to myself, “What is the intention behind me making this donation?” I make a lot of donations. The only reason I would make that donation was so Stevie Wonder would think I was nice. I said “no,” and I waited for him to say, "You nasty person!" You know what he said? He said, "Okay. Thanks a lot."

Cheryl: And what did that feel like in your body?

Oprah: It actually sat me down, that feeling that the world did not fall apart, and Stevie Wonder did not curse me out. He did not say, “I cannot believe it and now I'm going to write a song about how bad you are.” I thought, “Okay, that was not as bad as I thought.” And not only that, I felt powerful doing it.

Tune in next week for Part 2 of "The Power of No." New episodes of Dear Sugars are released weekly. Do you have a question for the Sugars? Email dearsugars@nytimes.com.